2-Nitroanisole

Chemical properties

yellow to amber liquid

Chemical properties

2-Nitroanisole is a yellowish or light-red to amber liquid. May be transported in molten form.

The Uses of 2-Nitroanisole

2-Nitroanisole is an intermediate in the synthesis of various potential therapeutic compounds.

The Uses of 2-Nitroanisole

2-Nitroanisole has been employed as solvatochromic probe to examine cybotactic region of pure and mixed supercritical fluid solvent systems.

Definition

ChEBI: A member of the class of 2-nitroanisoles that is anisole in which one of the hydrogens ortho to the methoxy group is replaced by a nitro group.

Production Methods

Methanolic sodium hydroxide is added slowly to a solution of 2- chloronitrobenzene in methanol at 70 ℃; the mixture is then heated gradually to 95 ℃ under pressure to complete the reaction. After dilution with water the product 2-Nitroanisole is separated as an oil, in 90 % yield, and methanol is recovered from the aqueous layer.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 4501, 1988 DOI: 10.1016/S0040-4039(00)80531-6

General Description

2-Nitroanisole (2-methoxynitrobenzene is an industrial and environmental pollutant causing tumors of the urinary bladder in rats and mice. Tumorigenic potential of 2-nitroanisole has been evaluated by host-mediated in vitro and in vivo assay.

Hazard

Questionable carcinogen.

Safety Profile

Confirmed carcinogen. Moderately toxic by ingestion. Mutation data reported. Explosive reaction with sodium hydroxide + zinc. Vigorous reaction with hydrogen + catalyst (at 250°C/34bar). When heated to decomposition it emits toxic fumes of NOx. See also p- NITROANISOLE.

Potential Exposure

A dye intermediate and for synthesis of other chemicals. NFPA has reported an explosion on during reduction with a nickel catalyst. Occupational exposure to 2-nitroanisole may occur through inhalation and dermal contact with this compound at workplaces where the chemical is produced or used.

Carcinogenicity

o-Nitroanisole is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN2730 Nitroanisoles, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3458 Nitroanisoles, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Purify it by repeated vacuum distillation in the absence of oxygen. [Beilstein 6 IV 1249.]

Incompatibilities

A strong oxidizer. Incompatible with strong acids; sulfur, combustibles, organics, and other easily oxidizable materials. Will accelerate the burning of combustible materials. If large quantities are involved in a fire or the combustible material is finely divided, an explosion may result. Prolonged exposure to fire or heat may result in an explosion. Explodes at temperatures ＞110℃. Combustible-liquid or fine powder may form explosive mixture with air. Nitroanisole reacts explosively with (sodium hydroxide ＋ zinc). It reacts vigorously with hydrogen1 catalyst (@ 250℃ & 25,500 mmHg).

Waste Disposal

Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.